Saturday, December 6, 2025

Going All-In on MSTR – A Wealth of Frequent Sense

A reader asks:

Let’s say I’ve a brother. Let’s say he was on a fortunate scorching streak this 12 months YOLO’ing into essentially the most speculative performs available in the market (quantum, crypto, meme shares, and many others) and was up 100% YTD. Urgent his luck, he thought it was a good suggestion to place practically all of his portfolio into MSTR (utilizing margin for extra leverage) when it was buying and selling within the 300’s and he’s now down 50%. I instructed him to by no means contact MSTR with a 10-foot pole and if he was bullish Bitcoin, simply purchase Bitcoin. I additionally instructed him many occasions to by no means use margin, particularly on excessive danger shares. He’s susceptible to a big % of his internet value (>50%) going away perpetually with a house buy on the horizon as effectively that’s in jeopardy. Now he all of a sudden desires my recommendation on learn how to get out of this mess. I instructed him I don’t know and I actually don’t. It’s a darned if you happen to do, darned if you happen to don’t lesser of two evils scenario. How do you take care of shoppers that persistently ignore your recommendation and now need your assist getting out of a large number?

I’ve a variety of ideas right here however first a narrative.

I roughly gave up watching baseball a decade or so in the past. It was too boring, the video games had been too lengthy and I had different stuff happening in my life.

However I obtained into the playoffs this 12 months for the primary time shortly. The Tigers gave the Mariners every thing they may deal with. Then the Mariners-Blue Jays collection went all the way down to the wire too. Otani is a modern-day Babe Ruth. And the Dodgers-Blue Jays performed probably the greatest World Sequence and video games 7s of my lifetime.

The lead analyst for MLB playoff video games on Fox is John Smoltz.

Listening to Smoltz discuss for therefore many video games jogged my memory that he virtually grew to become a shopper of a agency I used to work for.

The consulting agency I labored for proper out of faculty managed cash for institutional buyers however we had a handful of particular person shoppers. Smoltz is from Detroit and was truly drafted by the Tigers earlier than they stupidly traded him to the Braves.

Someway that Michigan connection led him to be really useful to our agency. My boss gave his individuals a tough no.

The aftermath of that call regarded one thing like this:

Me: Wait what?! Why would we not take this assembly?!

My boss: I labored with knowledgeable athlete previously, and I’m by no means doing it once more. It was a nasty expertise.

Me: But it surely’s John Smoltz!

My boss: It doesn’t matter who it’s. I solely need to work with sure sorts of shoppers. We are able to’t save everybody.

I used to be younger and didn’t perceive the reasoning however I do now. My previous boss knew nothing about John Smoltz however he had onerous and quick shopper match guidelines to save lots of himself time and power, even when it meant generally passing on doubtlessly good shoppers.

He didn’t need to spend his time attempting to save lots of shoppers from doubtlessly dangerous monetary selections.

Which brings us to the brother who put half of his life financial savings into Technique (MSTR) shares…utilizing margin…for cash that must be used to purchase a home!

I cringed extra with every phrase I learn on this query. It’s like a Russian doll of funding errors.

That is the issue with the bull market mind you get from making massive beneficial properties within the markets. It’s troublesome to know if you happen to’ve morphed right into a degenerate gambler whenever you’re getting cash. Traders who’ve taken on extreme ranges of danger the previous few years have been compensated for it.

When you get a few massive wins beneath your belt it’s straightforward to let issues get uncontrolled.

Technique (previously Microstrategy) was within the $300s when the brother obtained into the inventory. Now it’s effectively beneath $200 and falling quick:

Going All-In on MSTR – A Wealth of Frequent Sense

The inventory is now down greater than 63% from the highs:

This can be a 2008-level crash in a matter of months.

Right here’s the factor — I don’t know if Michael Saylor’s bitcoin experiment will work or not. It’s already labored higher than anybody might have exptected. Regardless of current losses the inventory continues to be up greater than 900% over the previous 10 years.

The issue is that this man’s brother wasn’t round for these beneficial properties. He’s solely taken half within the losses.

These beneficial properties got here with a variety of danger too. Simply take a look at the drawdown profile over the previous 10 years:

You’re taking a look at a 20% drawdown. A 50% drawdown. A 90% drawdown! A 46% drawdown. And now a 60% drawdown.

Michael Saylor’s experiment should work out. If Bitcoin resumes its uptrend, it’s potential Technique will too. Even when it does, I can’t condone placing 50% of your internet value within the inventory.

Technique is a levered play on Bitcoin as a result of Saylor is borrowing cash to purchase crypto. However then your brother borrowed cash as effectively? And he wants the home for a house buy?

This can be a Dumb & Dumber scenario:

Right here’s the factor — you can attempt to supply wise recommendation. Promote now earlier than it will get worse and also you get an enormous margin name. Put money into one thing way more cheap and diversified.

I’m undecided it’s going to matter.

After I first began my weblog I had this dream that I might one way or the other save individuals from making illogical monetary selections. After creating monetary content material for greater than a decade now I’ve come to appreciate this however some individuals can’t be saved.

They’re doomed to earn money mistake after cash mistake and there’s nothing you are able to do about it.

Then there are others who have to make an enormous mistake earlier than having an ah-ha second of realization that they should change their conduct. Some individuals do change their stripes but it surely’s not straightforward.

Can your brother be saved?

Perhaps.

He doubtless wants another person to take the steering wheel like a member of the family or advisor.

It’s one factor if you happen to’re YOLO buying and selling as a youngster with out a variety of duties. I don’t condone degenerate conduct, however younger individuals have loads of time and human capital to make up for early errors.

However if you happen to’re YOLOing cash that’s meant for a brand new home?!

You’ve got an issue.

You both put your portfolio on autopilot or hand the keys to knowledgeable in that case.

I’m afraid this man received’t study his lesson till he will get margin-called.

We coated this query on the most recent version of Ask the Compound:



Invoice Candy was on the present once more this week to assist me reply questions on promoting in a tax-efficient method with massive capital beneficial properties, Roth 401ks, paying for a house reworking venture, Roth conversions and HSAs.

Additional Studying:
Ben Graham & Bull Market Mind

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